6-iodo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 77969-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 6-iodo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• 英文别名: 9-iodo-7,8-dimethoxy-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 77969-39-2
• 化学式: C₁₈H₂₀INO₂
• 分子量: 409.267
• InChiKey: MXYVWZVVEWGGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-iodo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 、 苯乙炔 在 sodium hydroxide 、 palladium diacetate 作用下， 以 水 、 丙酮 为溶剂， 反应 30.0h， 以45.7%的产率得到7,8-dimethoxy-1-phenyl-6-(phenylethynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Synthesis of 6-substituted 1-phenylbenzazepines and their dopamine D1 receptor activities

  摘要：

  A series of racemic 6-aryl substituted 1-phenylbenzazepines 7a-e, and 17a,b were prepared. All these compounds showed binding potencies compatible to or much higher than that of the prototypic (+/-)-SKF- 38393 ((+/-)-1) and (+/-)-SKF-83959 (3) for the D(1) receptor. Among analogs of (+/-)-SKF-38393, compounds 7b, 7c and 7e possess 10-, 2- and 7-fold enhancement in binding for the D(1) receptor, respectively. Lower but compatible potency to that of (+/-)-1 was observed for compounds 7a and 7d. The optimal 6-substituents (m-tolyl, and 2 '-naphthyl) were applied to the skeleton of (+/-)-SKF-83959 (3). The resulting compounds 17a, b displayed high affinity at the D(1) receptor, only slightly lower than that of (3). These two compounds also showed good binding at the D(2) receptor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.049
• 作为产物：
  描述：

  6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 在 三氟乙酸酐 、 正丁基锂 、 碘 作用下， 以 二氯甲烷 、 乙醚 、 正己烷 为溶剂， 反应 3.67h， 以56.5%的产率得到6-iodo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Synthesis of 6-substituted 1-phenylbenzazepines and their dopamine D1 receptor activities

  摘要：

  A series of racemic 6-aryl substituted 1-phenylbenzazepines 7a-e, and 17a,b were prepared. All these compounds showed binding potencies compatible to or much higher than that of the prototypic (+/-)-SKF- 38393 ((+/-)-1) and (+/-)-SKF-83959 (3) for the D(1) receptor. Among analogs of (+/-)-SKF-38393, compounds 7b, 7c and 7e possess 10-, 2- and 7-fold enhancement in binding for the D(1) receptor, respectively. Lower but compatible potency to that of (+/-)-1 was observed for compounds 7a and 7d. The optimal 6-substituents (m-tolyl, and 2 '-naphthyl) were applied to the skeleton of (+/-)-SKF-83959 (3). The resulting compounds 17a, b displayed high affinity at the D(1) receptor, only slightly lower than that of (3). These two compounds also showed good binding at the D(2) receptor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.049

文献信息

• US4160765A
  申请人：——

  公开号：US4160765A

  公开（公告）日：1979-07-10
• US4255422A
  申请人：——

  公开号：US4255422A

  公开（公告）日：1981-03-10
• US4359464A
  申请人：——

  公开号：US4359464A

  公开（公告）日：1982-11-16